Halogenated naphthazine dyes



, Germany,

Patented May 19, 1925.

,UNITED, STATE PATENT" ornce.

WILHELM HERZBERG, OF BERLIN-WILMERSDORF, GERHARD HOPPE, OF BERLIN- TREPTOW, AND HEINRICH OHLEN'DORF, OF BERLIN-FRIEDENAU, GERMANY, AS- SIGNORS TO ACTIEN GES ELLS CHAFT FUR, ANILIN FABRIKATION, OF BERLIN, GER- Nu Drawing;

To all. whom it may concem 1 Be it known that we, E IL L l-Innznnne, GERHARD Horns, and HEINRICH OHLnNnonr, citizens ofthe German Republic, residing at- Berliu-lVilmersdorf, Germany, 3 Berlin- Treptow, Germany, and Berlin'Friedenau, have invented] certain new ant in Halogenated useful Improvements Naphthazine Dyes, of which thefollowing is a specification. I

By this invention the products obtained by fusing 8-sulfonicacid derivatives of a naphthazine of the general formula (R meaning an aryl residue) with alkalies furnish valuable dyestuffs when treated with halogenating agents; the products of reaction containing at mostffour atoms of 100 parts of nitrobenzene at a temperature of 50 C. gTo the solution 8 parts of sulfuryl chloride are slowly added. The reaction having come to anend, the nitroben= zene is distilled with steam. A trichloroderivative is obtained in this mannerwhich crystallizes in the form of yellow needles,

dissolves in concentrated sulfuric acid to a blue solution and is" decomposedat a temperature of about 250 C. When heated in an alkaline solution of-hydrosulfite it forms a yellow vat, from which cotton is dyed golden yellow tints, which become brighter after chlorination and areveryv fast I to light. i

Example 2. 5 parts of the parent materialused in Example 1 are dissolved in t 100 parts of nitrobenzene. Whilst stirring,-

10 parts of bromine are allowed to run slowly into the solution at a temperature of'100 acid of 'nAtooENArnn INAPHTHAZINE DYES.

i Application filed August 22, 1924. Serial No. 733,658.

- C. ;To finish the reaction the solution is heatedto'130 C. After distilling the nitrobenzene with steam the tribromo-compound is obtained in the form of brownish yellow needles, dissolving in concentrated sulfuric acid to a blue solution and melting at about 1 300 C. In a finely subdivided state the dyestuffmay be applied as a pigment; it has a golden yellow colour and is very fast to the action of light.

Example 3. 82 parts of the product of reaction obtained by fusing 1.2.1.2-dinaphthazine-8.8-disulfonic acid with an alkali are treated in 50 parts of nitrobenzene with parts of sulfuryl chloride at a temperature of 100 C. the temperature being raised finally to 140 C. After cooling, the product of chlorination separates in form of red needles, and is filtered off. It dissolves in concentrated sulfuric acid to a blue solution; it is insoluble in a solution of sodium hydroxide and soluble in slight degree in an alkaline solution of hydrosulphite.

By substituting in the foregoing example for the sulfuryl chloride 70 parts of bromide, a bromo-derivative is obtained which crystallizes in the form of dark red needles; when pulverized it forms a bluish red powder having the same properties as those of the product described in Example 3. g

If in the foregoing example the parent material is sulfonated before halogenation and the sulfonic acid or acids are treated in an aqueous solution w1th halogen, the latter is substituted for the sulfonic acld groups.

- .What we claim is,,-

, 1. A halogenated product containing at most four halogen atoms derived from a compound made by fusing an S-sulfonic a naphthazine of the general formula (R meaning an aryl residue) with alkali.

2. A halogenated product containing at 3. A halogenated product containing at most four halogen atoms derived from a most -four halogen atoms derived from the compound made by fusing an 8-sulfonic acid compound made by fusing 1.1.2.2-dinaphof a dinaphthazine of the general formula thazine-S.8-disulfonic acid with an alkali. 20

6 4. The new d e made 1) introducin four atoms of bromiiie into th e compound made l by fusing 1.1.2.Q-dinaphthazine-8.8.-disultonic acid With alkali. Na s In testimony whereof We aflix our si na- 10 Y tures in presence of two witnesses.

' \VI'LHELM HERZBERG.

GERHARD HOPPE. HEINRICH OHLENDORF.

Witnesses: (X meaning an univalent radical) with an FRED INDEN,

alkali. ROGER L. AUSPALL. 

